Triethylamine → 4-[(4-Nitrophthalimido)methylthio]pyridine

HRID 274689Notes

Reaction equation

HRID 274689 reaction equation
Cl[CH2:2][N:3]1[C:7](=[O:8])[C:6]2=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=[C:5]2[C:4]1=[O:16].[SH:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>C(O)C>[N+:13]([C:10]1[CH:9]=[C:6]2[C:7](=[O:8])[N:3]([CH2:2][S:17][C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[C:4](=[O:16])[C:5]2=[CH:12][CH:11]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3016883N-Chloromethyl-4-nitrophthalimide [for HPLC Labeling]HCID 178418431pyridine-4-thiol

Product 1

HCID 190791754-[(4-Nitrophthalimido)methylthio]pyridineYield 63.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-Chloromethyl-4-nitrophthalimide [2.89 g (12 mmol)] was added under ice-cooling with stirring to a suspension of 1.11 g (10 mmol) of 4-mercaptopyridine and 1.4 ml (12 mmol) of triethylamine in 50 ml of ethanol. The mixture was stirred at room temperature for 16 hours. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate) to obtain 1.99 g of the desired compound (yield: 63.1% yellow crystals).

Workup

  1. temperaturecooling
  2. distillationThe solvent was distilled off
  3. customthe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-d95ac0e361034769a5773b174684210c
Source dataset
uspto-grants-1995_02
Patent number
US05389658

Reaction notes

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